Observations in Hypergamy

I was flying to one of my army schools. It’s always fun to be on a flight booked by government funds. It feels like a mission... even if it is just a run of the mill educational experience in my case. But there is this undeniable undercurrent of excitement and purpose, giving me the feeling I’m being carried into something important and the unknown.

I was coming from DC and eventually headed to Georgia but we had a layover in Dallas. It was an early morning flight so the crowd on the plane were mostly business types; good-looking, well-dress people in their 30s to 50s on their way to or from some kind of meeting, golf-outing, what have you.

It was finally post-COVID and there wasn’t a single mask in sight. Nor the subtle tension that a group of humans create when one authoritarian looks to enforce some draconian policy.

Everyone was relaxed, in a good mood going about their business. There was even a feeling of gratitude to be simply doing normal things unimpeded by state-enforced nonsense.

The flight was uneventful as I utilized the time to get some solid reading and thinking done. Planes always make great fodder for meditations with the high-quality people watching and natural conditions for social experiments.

We began our descent into Dallas. The plane dropped in altitude, we hit the tarmac with a friendly little bump and skid, and proceeded to taxi to our gate. The flat, oppressive and dull terrain of the tarmac spread out before my gaze and on into the Texan sky.

I had the pleasure of sitting in a window seat and I looked dreamily out the window. I felt the anticipation of my coming school grow within me. I wondered about who I would meet, what I would learn, and in what ways would I be challenged.

Then out of the corner of my eye, the gentleman in front of me flipped out his iphone and popped off airplane mode.

He was a dapper dude, with a shimmering blue-grey golf polo of high-quality material and sharp-looking khakis with caramel colored shoes to match. He seemed to be some type of finance exec or C-suite mover and shaker. He was somewhere in his late 40s, probably early 50s. Maybe right on the cusp of the big half-century.

My eyes flicked back out the window but then were dragged once again to the space between the seat and plane where the gentleman’s phone was in full view. A cherry red app with a flame design logo grabbed my gaze like as if I was a Neanderthal spotting a bush of berries on a paleolithic stroll.

This man in front of me had just opened Tinder.

As soon as he got back to cell service, at approximately 8:30am, with no doubt greater responsibilities on his plate for that day, this man began swiping right and left like the best of college frat-bros. What’s more was; his age range setting would also be at home with the frat-bro demographic. As I saw the profiles stream by in rapid succession, they were all in their early 20s.

I was shocked. I had heard Jordan Peterson and others in the podcast domain talk about hypergamy before, but I never really knew anyone who ‘partook’ in it (with one exception, more of which later).  

But to see a guy whom if I passed in the airport I’d assume would be happily married (with three kids in various sports leagues or whatever) competing for the same girls in my dating pool blew my mind.

This was the definition of hypergamy made manifest.

Being completely honest, he wasn’t a particularly good-looking guy. He wasn’t the hunchback of Notre Dame by any means, but neither would he be gracing the cover of Men's Health anytime soon.

But with the amount of matches he was getting with beautiful 20-somethings it was plain to see that looks were not the only factor on the hypergamy-tilted playing field.

I realized in the moment that this was both a mild invasion of this guys privacy but also an incredible synchronicity of good fortune in observing these dynamics in Situ.

I took out my phone out and made some notes, of which I have since lost. But these few minutes where I watched this C-Suite gent rifle through dozens of beautiful 20-somethings in the greater Dallas-Fort Worth metro area, having more matches in a few minutes than I had had in the last month, has always stuck with me.

It was a fundamental revelation of a part of reality that I had not really known existed. Like in a video game, as if a whole portion of a map had been suddenly revealed whereas before I was walking with only a small circumference of my senses in front of me.

The experience was a confirmation that the playing field is indeed tilted in favor of those with advantages I simply do not have. It also showed me from an inverse perspective how I would be perceived by women my age who have both me and this guy in their Tinder chat DMs.

I always love to find the manifestation of inductive theories in real life. This was one of those times.

I had heard of the principle as an abstract concept of aggregate observation. But here was a perfect case study right in front of me at 8:30am on a flight from DC to Dallas.

As I sat back in my chair with a bemused grin on my face and ‘Son of Bitch’ ringing through my head, my mind started to ponder more broadly the reality of hypergamy I’d just witnessed.

Then another example of this phenomenon clicked instantly into resolution.

In high school, one of my best female friends was famous amongst our chattering, rowdy classmates for dating an older football player from a rival high school.

Her boyfriend was a star middle linebacker, with enormous muscles for an 18 year old and a full beard to boot (still a better beard than mine now). People often joked that he was on steroids and actually, he may have been given the phenotypic expression of muscles.

I digress.

Later in college, before this same friend and I fell out of contact, she told me about how she was using a sugar-daddy website.

This website was one where older, wealthy men could take young women on dates in exchange for gifts. These gifts could consist of anything from expensive purses to salon visits to week-long companionship trips to luxury destinations like Dubai.

All of which my friend confided in me she had received.

When she first told me this I was amazed and shocked. But the shock soon gave way to a more grim, amused satisfaction of the kind when you find out something unpleasant you suspected is indeed true.

And now in light of this gentlemen in front of me, and reviewing the pattern of my friends dating history, the principle emerged in stark clarity.

Even more confirming were the details my friend shared with when I asked the juicy and controversial question; if sex was ‘expected’ on these dates.

What she said surprised me and humanized my sense of the entire interaction by a significant degree.

The way she described it I was left with the impression that these guys may even have been on the spectrum to a slight degree. It may be confirmation bias, but it does seem to square that guys who would be really good at widgetizing themselves for work with minimal social skills would face problems in dating.

She told me that most of these men were hyper-ambitious career guys. They had dedicated everything to their work life and by the time they looked up to start to date, they were 35 or 40 with almost zero dating experience.

This made them awkward and naïve about the whole thing.

But the one asset they did have in abundance was money.

And thus, a natural arrangement of capitalism (a need in the market place if you will) was born.

So, my friend got to go on expensive trips with bougie purses because these fellas did the ‘right’ thing and put their nose to the grindstone for 60-80hrs a week for 15 years.

Ergo, we can see hypergamy as an exchange of advantageous resources between two parties.

One has time, charm, feminine graces and if we’re being completely honest (but still tasteful) ‘availability’. My friend was and is; gorgeous, sensitive, hilarious and literarily inclined. She’s a catch to anybody.

The other has money, access, social prestige and the accrued wisdom of simply living longer and attaining a modicum of success in a certain field.

If I had to guess I’d wager there are broadly two camps of these types of fellas:

One; the unrepentant high-roller bachelor who wants companionship without the strings attached. He’s probably a jet-setter with meetings in London Monday through Wednesday but he needs to be in LA at by the end of the week. Maybe he’s recently divorced or maybe his ambition never allowed him to settle down.

The other type, I would surmise, is likely hyper-studious and possibly on the spectrum. He’s probably a computer engineer or a lawyer; highly adapted to a lifestyle of high-hourly drudgery under halogen lights. He’s his boss's cash cow; hard-nosed and expert at his domain of skills but perhaps a bit of a push-over in the realm of office politics. He was always a great student and identifies deeply with ‘Getting A's’ as a way to relate to the entire world around him.

Regardless of the specifics, hypergamy is very much a thing in the modern dating scene.

Now, I do not write any of this with a sense of judgment or condemnation.

The only thing that comes close to that for me is a sense of indignant unfairness at the discovery that not only am I competing with all the studly, wizardly, highly competent guys my own age - but also the numerous others with reams more advantages in the preceeding generations on the prowl.

I guess part of me wants an ideal world where each age cohort dates strictly within their own and there’s no real overlap. I realize this is pretty wishful and am comfortable letting it go, except in perhaps the most egregious of cases.

On the other hand, I’m a firm believer that the right one will come along when you’re ready for it. There are some caveats to that belief that reality has drilled into me. But generally, it does seem true that two people who are seriously looking to find a long-term significant other and are willing to be clear-eyed, honest and diligent about making it happen, will more than likely make it happen.

But for the naïve and uninitiated (like my former self) it is highly pertinent to understand hypergamy. At least on a personal level.

If you’re going out into the dating game, it’s not just you and your sloppy college buddies or work colleagues. If you want to bring a high-value, high-functioning partner into your life and keep them (which you probably do given that this makes life way better overall, for you and all your relationships) then you need to know the full contours of the playing field. Otherwise, you’re fighting in the dark with one hand tied behind your back.

To this end, once one is fully aware of the big picture, there is a seemingly positive effects to personally evolve through competition pressure. If I know I’m competing with a 45-year-old CEO type then I need to step up my game if I want to get the girl.

Whether that is fair or not is a separate question.

It could also be argued that it’s too difficult to compete with that type of person as a young man.

Perhaps that’s right. But that seems to come from a scarcity-based perception of the world and belies the reality of the synchronicity of mutually concerted purpose (that might be a law of reality right there, TM*).

In other words; what I said earlier about two people wanting to be together and make it work, barring any catastrophic variables.

On a societal level, I am first and foremost highly reticent to offer any proscriptive and/or moralizing commentary.

I think in the realm of romantic endeavor to impose too much top-down ideals on what ‘should’ be is generally bound to backfire.

On the other hand, I am aware of and basically optimistic about, the resurgence of (usually) religion-based dating communities that support and softly enforce monogamy through social cohesion and pressure. But this, in my opinion, must be based on radical transparency and on a strict voluntary basis only.

Otherwise, it will definitely backfire. Scarlet letters, witch trials and cult leaders with other people’s wives are clear examples of that.

But for the purposes of our enquiry, on a societal level it seems it could be a natural counterbalance against the more destructive versions of hypergamy gone awry.

In the end, it’s not necessarily evident to me that hypergamy is a problem. It just seems to be one of those topics that’s difficult to discuss with ‘polite’ society at a dinner table. On the other hand it is a very real phenomenon, and likely (though I have no aggregate data to prove it) more common now than ever given the correlating reality of no-fault divorce and the democratization of sex.

All told it’s been fun to write about and I would love to know what your thoughts, experiences and comments are on the subject. Shoot me an email.

Thank you for reading. My best to you and much love. 😊.